http://rdf.ncbi.nlm.nih.gov/pubchem/patent/AR-085020-A1
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_648c9679dd9ec36125406a2dafa6bf7e |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D213-78 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D213-79 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D213-81 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D213-803 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D213-84 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D213-61 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D213-81 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D213-79 |
| filingDate | 2012-01-24-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 2013-08-07-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | AR-085020-A1 |
| titleOfInvention | PROCESS TO PREPARE 4-AMINO-5-FLUOR-3-HALO-6- (REPLACED) PICOLINATES AND INTERMEDIARIES OF SUCH SYNTHESIS |
| abstract | Claim 1: A process for the preparation of a 4-amino-5-fluorine-3-halo-6- (substituted) picolinate of the formula (1) wherein W represents Cl, Br or I; R represents C1-4 alkyl, cyclopropyl, C2-4 alkenyl or phenyl substituted with from 1 to 4 substituents independently selected from the halogen, C1-4 alkyl, C1-4 haloalkyl, C1-4 alkoxy or C1-4 haloalkoxy; and R1 represents C1-12 alkyl or an unsubstituted or substituted C7-11 arylalkyl; comprising the following steps: a) fluoridation of 4,5,6-trichloropicolinonitrile of formula (A) with a source of fluoride ion to produce 4,5,6-trifluoropicolinonitrile of formula (B); b) the amination of 4,5,6-trifluorpicolinonitrile of formula (B) with ammonia to produce the 4-amino-5,6-difluoropicolinonitrile of formula (C); c) the hydrolyzing of the substituent nitrile and exchange of the substituent fluorine in the 6-position of 4-amino-5,6-difluoropicolinonitrile of formula (C) with an iodine, bromine or chlorine substituent by treatment with an iodide source, bromide or chloride to produce a 4-amino-5-fluorine-6-halopicolinamide of the formula (D), wherein X represents Cl, Br or I; d) esterification of the 4-amino-5-fluorine-6-halopicolinamide of the formula (D) with an alcohol (R1OH) and a Bronsted or Lewis acid to produce a 4-amino-5-fluorine-6-halopicolinate of the formula (E) wherein R1 represents C1-12 alkyl or an unsubstituted or substituted C7-11 arylalkyl; e) the halogenation of the 4-amino-5-fluorine-6-halopicolinate of the formula (E) with a halogen source to produce a 4-amino-5-fluorine-3,6-dihalopicolinate of the formula (F), wherein W and X independently represent Cl, Br or I, and R1 is as previously defined; and f) coupling the 4-amino-5-fluorine-3,6-dihalopicolinate of the formula (F) with an aryl, alkyl or alkenyl metal compound of the formula: R-Met, wherein R is as previously defined and Met represents a Zn-halide, Zn-R, tri- (C1-4 alkyl) tin, copper, or B (OR2) (OR3), where R2 and R3 are independent of each other, hydrogen, C1- alkyl 4, or when taken together they form an ethylene or propylene group in the presence of a transition metal catalyst, to produce the 4-amino-3-halo-5-fluorine-6- (substituted) picolinate of the formula (1 ). |
| priorityDate | 2011-01-25-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
Total number of triples: 52.